Guadalupetown, Cáceres provincia (province), in the Extremadura comunidad autónoma (autonomous community), southwestern Spain. It lies on the southeastern slopes of the Guadalupe Mountains near the Guadalupejo River east of Cáceres city. The town is famous for its monastery, which had its origins as a small hermitage built in the early 14th century on the spot where a shepherd had found an image of the Virgin. This shrine became known as Our Lady of Guadalupe and became a centre of pilgrimage. Alfonso XI of Castile visited the shrine in 1337, and in 1340 he founded a monastery there. In 1389 the Hieronymites (Hermit Order of St. Jerome) took over the monastery, and their first prior built the church with its Moorish-style cloisters and hospices; later, Henry IV of Castile and his mother, María of Aragon, were entombed there. The Flamboyant Gothic chapel of Santa Ana, the Gothic cloister, the chapter hall, and the library were added to the monastery later. The monastery was designated a UNESCO World Heritage site in 1993.

The monastery of Guadalupe became one of the wealthiest and most important in Spain and achieved great renown for its architectural splendour and its artworks and other treasures. The monks there were skillful miniaturists, ironworkers, and silversmiths, and their surviving works are on display along with some notable paintings by Francisco de Zurbarán and Luca Giordano. The monastery was abandoned after monasteries were secularized in 1835 but was occupied by the Franciscans in 1908.

The modern-day town retains its function as a pilgrimage centre and serves as a market for cheese, vegetable oils, chestnuts, and cork. Goat breeding is significant in the surrounding areas. Tourism has increased in importance. Pop. (20052007 est.) mun., 2,227113.